Acetic Acid → HCID 86761415, compound

HRID 912710Notes

Reaction equation

HRID 912710 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH:9]([CH3:12])[CH:10]=O.N[C:14]1[NH:18][CH:17]=[N:16][C:15]=1[C:19]([NH2:21])=[O:20].C(O)(=O)C.C([BH3-])#[N:27].[Na+]>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH:9]([CH3:12])[CH2:10][NH:27][N:16]1[C:15]([C:19]([NH2:21])=[O:20])=[CH:14][N:18]=[CH:17]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 5003444Sodium cyanoborohydride2×HCID 86631142HCID 86631142, compound

Product 1

HCID 86761415HCID 86761415, compound

Procedure

The title compound was prepared in accordance with the general method described in Example 17(e) using 2-(pyridin-2-ylmethoxy)-propanal (0.875 g, 5.30 mmol, obtained from Example 20(b)), 5-aminoimidazole-4-carboxamide (0.668 g, 5.30 mmol), acetic acid (0.61 mL, 10.6 mmol) and sodium cyanoborohydride (0.666 g, 10.6 mmol) with the exception that the solution of aldehyde and carboxamide was stirred for 1 h and that sodium cyanoborohydride was added after 15 min. This yielded 1.32 g of the title compound, which was used in the next step without purification. MS (ESI) m/z 276 (M+1).

Workup

  1. customThis yielded 1.32 g of the title compound, which was used in the next step without purification

Sources & evidence

ORD record
ord-d9580cf2d81340fe8f0cfeccda7f46b4
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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